Too often we encounter a Director of Development or an MGO who is just exasperated with the CEO or Executive Director of their nonprofit because they don’t want anything to do with major gifts.
Richard and I hear story after dreadful story from development professionals like you who feel they are leaving hundreds of thousands… or even millions of dollars on the table because their CEO or ED will not do their job.
As you know, you need your leader to be engaged with it. Not only you – your donors need it, too.
If your donors are going to make a significant investment in your organization, they want access to leadership.
But what do you do when that leader is uncomfortable talking to, cultivating and soliciting donors? Here are some ways to help your CEO or ED not only get comfortable, but succeed in major gifts:

1. Listen — The first step is to sit down with your CEO and listen to her story. Ask questions that will help you understand why and where her discomfort is. Many times there has been a bad experience around money or a donor that has shut her down. Try to figure out the root of the problem. Then address it with compassion and understanding. Richard and I have seen CEOs turn around their anxiety just by talking it through, with someone helping them understand what the donors need from them.
2. Educate — Many times I hear a CEO or ED talk about not wanting to “bug” a donor because it will offend donors to ask them for money. This is an obvious misconception that leaders latch onto because they feel uncomfortable about it themselves. So they create a story to justify their inaction. Your job is to present them with data. Show them your donor file and the potential your donors have to give to your organization. Pass on articles written by nonprofit CEOs who embrace major gift fundraising and tell why they do. If you have donors with whom you have a good relationship, ask them to come in and talk to your CEO or ED about why donors need them to be engaged. Nothing would be more powerful than to have a donor speak directly to your CEO or ED about the importance of their leadership in major gifts.
3. Manage — Your job is to make major gifts as easy as possible. This is why you need to manage a small executive caseload of donors for your executive. In other words, take all the hard work out of it and tee up touches, lunches, and solicitations. To do this, give your ED or CEO a weekly “to-do” list and give him or her the background, contact info, etc. – so all they have to do is make the call or do the meeting. Leaders get distracted. They get even more distracted when they are uncomfortable with something. Your job is to keep them focused and on point. You need to meet with them on a weekly basis and keep them on task. Don’t allow them to go off somewhere without doing what they promised they would do.
4. Coach — Your CEO became CEO for a reason. He has great skills. Use those skills and turn them toward cultivating and soliciting donors. Obviously he has a passion for your mission. Take that passion and help him be a passionate ambassador with major donors. This will take practice, patience and more practice. Richard and I have sat with CEOs and EDs, and while it may take some time, they can be coached into becoming great storytellers and solicitors for major gifts.
5. Encourage — Nonprofit leaders are like all of us… they need to be praised and encouraged in their work. Many times I hear from CEOs or EDs that they often feel alone. I think that is a shame. Your job with a leader is always to encourage and look for “wins” for them. The best way to get a leader excited about major gifts is for her to experience first-hand a donor saying yes to her. Your job is to make that happen as often as possible until your CEO has “got it” and embraced major gifts as integral to her job.

Look, I’m not going to sugarcoat this. This is not easy. But Richard and I have seen so many leaders who seemed hopeless with major gifts, but then they had a complete turnaround and became great with donors.
Your job is to stick with it. There will be times you will be discouraged. Don’t give up. Your nonprofit needs you to keep moving forward.
If you have stories about how you helped your CEO or ED embrace major gifts, please share them with the Passionate Giving community. We want to hear your stories. If we like them, we may want to use them to help your colleagues inspire their leaders.
Jeff